↓ Skip to main content

Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1‑Substituted 1,2,3,4-Tetrahydroisoquinolines

Overview of attention for article published in Journal of Organic Chemistry, July 2014
Altmetric Badge

Mentioned by

twitter
1 X user

Citations

dimensions_citation
70 Dimensions

Readers on

mendeley
49 Mendeley
You are seeing a free-to-access but limited selection of the activity Altmetric has collected about this research output. Click here to find out more.
Title
Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1‑Substituted 1,2,3,4-Tetrahydroisoquinolines
Published in
Journal of Organic Chemistry, July 2014
DOI 10.1021/jo501099h
Pubmed ID
Authors

Elma Mons, Martin J. Wanner, Steen Ingemann, Jan H. van Maarseveen, Henk Hiemstra

Abstract

A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.

X Demographics

X Demographics

The data shown below were collected from the profile of 1 X user who shared this research output. Click here to find out more about how the information was compiled.
Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 49 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 49 100%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 15 31%
Student > Master 8 16%
Student > Bachelor 6 12%
Researcher 5 10%
Lecturer 2 4%
Other 5 10%
Unknown 8 16%
Readers by discipline Count As %
Chemistry 30 61%
Pharmacology, Toxicology and Pharmaceutical Science 2 4%
Biochemistry, Genetics and Molecular Biology 2 4%
Materials Science 2 4%
Computer Science 2 4%
Other 3 6%
Unknown 8 16%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 05 August 2014.
All research outputs
#20,657,128
of 25,377,790 outputs
Outputs from Journal of Organic Chemistry
#26,833
of 28,613 outputs
Outputs of similar age
#175,003
of 239,660 outputs
Outputs of similar age from Journal of Organic Chemistry
#82
of 109 outputs
Altmetric has tracked 25,377,790 research outputs across all sources so far. This one is in the 10th percentile – i.e., 10% of other outputs scored the same or lower than it.
So far Altmetric has tracked 28,613 research outputs from this source. They receive a mean Attention Score of 4.5. This one is in the 2nd percentile – i.e., 2% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 239,660 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 14th percentile – i.e., 14% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 109 others from the same source and published within six weeks on either side of this one. This one is in the 6th percentile – i.e., 6% of its contemporaries scored the same or lower than it.